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Dimethylacetamide → 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

HRID 522257
Notes
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Reaction equation

HRID 522257 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C[C:23]([N:25](C)C)=O.Cl[C:29]1[N:37]=[C:36]2[C:32]([N:33]=[CH:34][N:35]2[CH3:38])=[C:31]([C:39]2[CH:44]=[CH:43][C:42]([O:45]CC3C=CC(OC)=CC=3)=[C:41]([C:55]([F:58])([F:57])[F:56])[CH:40]=2)[N:30]=1>[Zn].[C-]#N.[Zn+2].[C-]#N.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.O>[OH:45][C:42]1[CH:43]=[CH:44][C:39]([C:31]2[N:30]=[C:29]([C:23]#[N:25])[N:37]=[C:36]3[C:32]=2[N:33]=[CH:34][N:35]3[CH3:38])=[CH:40][C:41]=1[C:55]([F:56])([F:57])[F:58]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 31374DimethylacetamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 1178996942-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine

Product 1

HCID 1370152256-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

Reagents, catalysts & solvents 4

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst
HCID 23994ZincCatalyst
HCID 2733347Palladium(II) trifluoroacetateCatalyst
HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Zinc (64 mg), 2-(di-tert-butylphosphino)biphenyl (163 mg), zinc cyanide (230 mg), and palladium (II) trifluoroacetate (81 mg) were added to a DMAc (16.5 mL) solution of 2-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine (1.1 g) at room temperature in an argon atmosphere, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, then extraction thereof was performed using EtOAc, and the extract was washed with water. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby a mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile and 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile (502 mg) was obtained.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washthe extract was washed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby
  8. additiona mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile

Sources & evidence

ORD record
ord-9ae48241993d4c53bf1f34d515d62172
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328118B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes